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When is a tax accountant also a relationship counselor? When your boyfriend 1099's you. Howard Shih is involved in tax court proceedings over the questionable use of the term "wages" to refer to payments he made to his girlfriend in 2005. Jue-ya Yang moved into his house at some point during the year, and though she had no skills or experience pertaining to his work (as an artist and calligrapher), Howard noted on checks he gave her for spending money "salary" or "wages."

That should have been her first clue. Later, he reported the money he'd paid her, $10,500 in all, on a 1099-MISC form. Eventually Yang was asked to pay taxes on that $10,500 (and another $40,000 of unreported income that she didn't dispute, did she have other boyfriends for whom she did work, I wonder?), and complained to the tax commissioner that the money from Shih was, in fact, a gift.

Tax court ruled in her favor, though she still owes taxes on the $40,000 not in dispute. There is no evidence of why the two broke up; I'm thinking irreconcilable tax brackets may have been a factor.

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TurboTax Articles

It's been said by many that looking for a job is a job in itself. The Internal Revenue Service (IRS) allows the deduction related to some costs of job hunting, the same way employees can deduct some unreimbursed job expenses. Not all job searches qualify, though, so it's wise to educate yourself on the rules.

The Affordable Care Act, or Obamacare, requires certain employers to offer health insurance coverage to full-time employees and their dependents. Further, those employers must send an annual statement to all employees eligible for coverage describing the insurance available to them. The Internal Revenue Service (IRS) created Form 1095-C to serve as that statement.

If you paid interest on a qualified student loan, you may be able to deduct some or even all of that interest on your federal income tax return. Student loan companies use IRS Form 1098-E to report how much you paid in interest. Borrowers get a copy of this form, and so does the IRS.